ES2204555T3 - Procedimiento mejorado para la preparacion de sales no higroscopicas de l(-)-carnitina. - Google Patents
Procedimiento mejorado para la preparacion de sales no higroscopicas de l(-)-carnitina.Info
- Publication number
- ES2204555T3 ES2204555T3 ES00920506T ES00920506T ES2204555T3 ES 2204555 T3 ES2204555 T3 ES 2204555T3 ES 00920506 T ES00920506 T ES 00920506T ES 00920506 T ES00920506 T ES 00920506T ES 2204555 T3 ES2204555 T3 ES 2204555T3
- Authority
- ES
- Spain
- Prior art keywords
- carnitine
- acid
- weight
- granulate
- powder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical class C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 29
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 22
- 239000008187 granular material Substances 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 15
- 239000002245 particle Substances 0.000 claims abstract description 11
- 238000007711 solidification Methods 0.000 claims abstract description 11
- 230000008023 solidification Effects 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000001530 fumaric acid Substances 0.000 claims abstract description 6
- -1 tartrate (-) - carnitine Chemical compound 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 239000000155 melt Substances 0.000 claims abstract description 3
- 230000008021 deposition Effects 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 229960004203 carnitine Drugs 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 abstract description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract description 3
- 239000001358 L(+)-tartaric acid Substances 0.000 abstract description 2
- 235000011002 L(+)-tartaric acid Nutrition 0.000 abstract description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 abstract description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000151 deposition Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000011837 pasties Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000011093 chipboard Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI990551 | 1999-03-19 | ||
| IT1999MI000551A IT1312018B1 (it) | 1999-03-19 | 1999-03-19 | Procedimento migliorato per la produzione di sali non igroscopicidella l(-)-carnitina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2204555T3 true ES2204555T3 (es) | 2004-05-01 |
Family
ID=11382333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00920506T Expired - Lifetime ES2204555T3 (es) | 1999-03-19 | 2000-03-16 | Procedimiento mejorado para la preparacion de sales no higroscopicas de l(-)-carnitina. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6372940B1 (cs) |
| EP (1) | EP1163207B1 (cs) |
| JP (1) | JP2002540094A (cs) |
| KR (1) | KR100664560B1 (cs) |
| CN (1) | CN1147462C (cs) |
| AR (1) | AR023101A1 (cs) |
| AT (1) | ATE247627T1 (cs) |
| AU (1) | AU4105800A (cs) |
| CA (1) | CA2359106A1 (cs) |
| CZ (1) | CZ299312B6 (cs) |
| DE (1) | DE60004649T2 (cs) |
| DK (1) | DK1163207T3 (cs) |
| ES (1) | ES2204555T3 (cs) |
| HK (1) | HK1042468A1 (cs) |
| HU (1) | HUP0200402A3 (cs) |
| IT (1) | IT1312018B1 (cs) |
| NZ (1) | NZ512640A (cs) |
| PL (1) | PL199614B1 (cs) |
| PT (1) | PT1163207E (cs) |
| SI (1) | SI1163207T1 (cs) |
| SK (1) | SK13312001A3 (cs) |
| WO (1) | WO2000056701A1 (cs) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2631569B1 (fr) * | 1988-05-20 | 1990-07-27 | Renault Automation | Detecteur de proximite magnetique destine notamment a la decoupe laser |
| ITRM20010030A1 (it) * | 2001-01-23 | 2002-07-23 | Aldo Fassi | Sali di carnitine utili come integratori dietetici/nutrizionali o come farmaci, composizioni che li contengono e procedimenti per la loro pr |
| SI1757606T1 (sl) * | 2001-02-24 | 2009-10-31 | Boehringer Ingelheim Pharma | Ksantinski derivati za uporabo kot zdravila kot tudi postopek za njihovo pripravo |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| DE102005035891A1 (de) * | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| EP2540725A1 (de) | 2006-05-04 | 2013-01-02 | Boehringer Ingelheim International GmbH | Polymorphe von 1-((4-Methyl-chinazolin-2-yl)methyl)-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-amino-piperidin-1-yl)xanthin |
| PE20080251A1 (es) * | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| CN101209975B (zh) * | 2006-12-29 | 2010-12-01 | 沈阳科硕营养科技有限公司 | 左旋肉碱富马酸钙及其制备方法与用途 |
| JP5769966B2 (ja) * | 2007-08-17 | 2015-08-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｆａｂ関連疾患治療用プリン誘導体 |
| PE20140960A1 (es) * | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| PE20100156A1 (es) * | 2008-06-03 | 2010-02-23 | Boehringer Ingelheim Int | Tratamiento de nafld |
| KR20200118243A (ko) | 2008-08-06 | 2020-10-14 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| WO2010018217A2 (en) * | 2008-08-15 | 2010-02-18 | Boehringer Ingelheim International Gmbh | Organic compounds for wound healing |
| US8513264B2 (en) | 2008-09-10 | 2013-08-20 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| MX2011006713A (es) | 2008-12-23 | 2011-07-13 | Boehringer Ingelheim Int | Formas salinas de compuesto organico. |
| AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
| CA2782179C (en) | 2009-11-27 | 2020-06-23 | Boehringer Ingelheim International Gmbh | Treatment of genotyped diabetic patients with dpp-iv inhibitors such as linagliptin |
| EP2566469B1 (en) | 2010-05-05 | 2022-12-21 | Boehringer Ingelheim International GmbH | Combination therapy |
| ES2953123T3 (es) | 2010-06-24 | 2023-11-08 | Boehringer Ingelheim Int | Terapia para la diabetes |
| EP2425834A1 (en) * | 2010-09-06 | 2012-03-07 | Lonza Ltd. | Process for the production of l-carnitine tartrate |
| JP2012092036A (ja) * | 2010-10-26 | 2012-05-17 | Mitsubishi Rayon Co Ltd | カルニチンの塩の製造方法 |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| DK2731947T3 (en) | 2011-07-15 | 2019-04-23 | Boehringer Ingelheim Int | SUBSTITUTED DIMERIC QUINAZOLINE DERIVATIVE, PREPARATION AND USE thereof IN PHARMACEUTICAL COMPOSITIONS FOR TREATMENT OF TYPE I AND TYPE II DIABETES |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| EP2849754B1 (en) | 2012-05-14 | 2022-09-14 | Boehringer Ingelheim International GmbH | Linagliptin, a xanthine derivative as dpp-4 inhibitor, for use in the treatment of sirs and/or sepsis |
| EP2849755A1 (en) | 2012-05-14 | 2015-03-25 | Boehringer Ingelheim International GmbH | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| US20140316156A1 (en) * | 2013-04-18 | 2014-10-23 | Deborah Warner | Method of producing therapeutic agent |
| JP6615109B2 (ja) | 2014-02-28 | 2019-12-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｄｐｐ−４阻害薬の医学的使用 |
| KR102391564B1 (ko) | 2016-06-10 | 2022-04-29 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴 및 메트포르민의 병용물 |
| CN106748845B (zh) * | 2016-12-23 | 2018-11-20 | 东北制药集团股份有限公司 | 一种左旋肉碱盐微粉的制备方法 |
| KR20190017310A (ko) | 2017-08-10 | 2019-02-20 | 주식회사 셀트리온화학연구소 | 약제학적 성질이 개선된 l-카르니틴 화합물의 염, 이의 제조방법, 이를 함유하는 약학 조성물 |
| JP6964876B2 (ja) * | 2017-11-27 | 2021-11-10 | 株式会社古川リサーチオフィス | オロット酸−カルニチン混合体粉体又はフマル酸−カルニチン混合体粉体の製造方法 |
| CN108383741A (zh) * | 2018-03-16 | 2018-08-10 | 开原亨泰化工有限公司 | 一种制备左旋肉碱成盐的新方法 |
| CN109096129B (zh) * | 2018-09-30 | 2021-04-27 | 东北制药集团股份有限公司 | 一种左旋肉碱酒石酸盐的制备方法 |
| CN109535022B (zh) * | 2018-11-12 | 2022-03-01 | 天津大学 | 一种提高左旋肉碱富马酸盐流动性的制备方法 |
| US20240217920A1 (en) * | 2022-12-28 | 2024-07-04 | Hubei Xujie Pharmaceutical Co., Ltd. | Process for producing l-carnitine |
| US20240228429A1 (en) * | 2023-01-04 | 2024-07-11 | Hubei Xujie Pharmaceutical Co., Ltd | Process for producing l-carnitine |
| CN118638020B (zh) * | 2024-08-08 | 2024-11-19 | 杭州海尔希畜牧科技有限公司 | L-天门冬氨酸l(-)肉碱(1:1)的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3463261D1 (en) * | 1983-12-28 | 1987-05-27 | Sigma Tau Ind Farmaceuti | Salts of l-carnitine and alkanoyl l-carnitines and process for preparing same |
| IT1172394B (it) * | 1983-12-28 | 1987-06-18 | Sigma Tau Ind Farmaceuti | Sali della l-carnitina e di alcuni alcanoil derivati della l-carnitina e procedimento per la loro preparazione |
| US5073376A (en) * | 1989-12-22 | 1991-12-17 | Lonza Ltd. | Preparations containing l-carnitine |
| IT1289974B1 (it) | 1997-02-25 | 1998-10-19 | Aldo Fassi | Procedimento per la produzione di sali stabili e non igroscopici di l(-)carnitina e di alcanoli l(-)-carnitine |
| AU718308B2 (en) * | 1996-05-31 | 2000-04-13 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Stable, non-hygroscopic salts of L(-)carnitine and alkanoyl L(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts |
-
1999
- 1999-03-19 IT IT1999MI000551A patent/IT1312018B1/it active
-
2000
- 2000-03-16 WO PCT/EP2000/002344 patent/WO2000056701A1/en not_active Ceased
- 2000-03-16 US US09/868,980 patent/US6372940B1/en not_active Expired - Fee Related
- 2000-03-16 DK DK00920506T patent/DK1163207T3/da active
- 2000-03-16 HU HU0200402A patent/HUP0200402A3/hu unknown
- 2000-03-16 CN CNB008034001A patent/CN1147462C/zh not_active Expired - Fee Related
- 2000-03-16 PT PT00920506T patent/PT1163207E/pt unknown
- 2000-03-16 PL PL349894A patent/PL199614B1/pl not_active IP Right Cessation
- 2000-03-16 EP EP00920506A patent/EP1163207B1/en not_active Expired - Lifetime
- 2000-03-16 SI SI200030176T patent/SI1163207T1/xx unknown
- 2000-03-16 JP JP2000606564A patent/JP2002540094A/ja not_active Ceased
- 2000-03-16 CZ CZ20013376A patent/CZ299312B6/cs not_active IP Right Cessation
- 2000-03-16 DE DE60004649T patent/DE60004649T2/de not_active Expired - Lifetime
- 2000-03-16 AT AT00920506T patent/ATE247627T1/de not_active IP Right Cessation
- 2000-03-16 KR KR1020017010602A patent/KR100664560B1/ko not_active Expired - Fee Related
- 2000-03-16 NZ NZ512640A patent/NZ512640A/xx unknown
- 2000-03-16 ES ES00920506T patent/ES2204555T3/es not_active Expired - Lifetime
- 2000-03-16 SK SK1331-2001A patent/SK13312001A3/sk unknown
- 2000-03-16 CA CA002359106A patent/CA2359106A1/en not_active Abandoned
- 2000-03-16 HK HK02104080.1A patent/HK1042468A1/zh unknown
- 2000-03-16 AU AU41058/00A patent/AU4105800A/en not_active Abandoned
- 2000-03-17 AR ARP000101222A patent/AR023101A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1147462C (zh) | 2004-04-28 |
| SI1163207T1 (en) | 2003-12-31 |
| HK1042468A1 (zh) | 2002-08-16 |
| ITMI990551A1 (it) | 2000-09-19 |
| SK13312001A3 (sk) | 2002-05-09 |
| AU4105800A (en) | 2000-10-09 |
| PL349894A1 (en) | 2002-09-23 |
| JP2002540094A (ja) | 2002-11-26 |
| ATE247627T1 (de) | 2003-09-15 |
| DK1163207T3 (da) | 2003-12-01 |
| CZ299312B6 (cs) | 2008-06-18 |
| EP1163207A1 (en) | 2001-12-19 |
| CN1339023A (zh) | 2002-03-06 |
| IT1312018B1 (it) | 2002-04-04 |
| KR100664560B1 (ko) | 2007-01-03 |
| HUP0200402A2 (hu) | 2002-05-29 |
| CZ20013376A3 (cs) | 2002-02-13 |
| KR20010102288A (ko) | 2001-11-15 |
| DE60004649T2 (de) | 2004-03-18 |
| PL199614B1 (pl) | 2008-10-31 |
| PT1163207E (pt) | 2003-12-31 |
| EP1163207B1 (en) | 2003-08-20 |
| HUP0200402A3 (en) | 2002-11-28 |
| CA2359106A1 (en) | 2000-09-28 |
| AR023101A1 (es) | 2002-09-04 |
| WO2000056701A1 (en) | 2000-09-28 |
| DE60004649D1 (de) | 2003-09-25 |
| NZ512640A (en) | 2003-03-28 |
| US6372940B1 (en) | 2002-04-16 |
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